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If a riddle has multiple possible answers, then it has a greater chance of being solved. And when you're up against a master of riddles, the fewer possible answers you can give her, the better your chances are of stumping her.
What is the thing that in order to have, you must give it up? There is one answer: the answer to an impossible riddle. An elegant solution from Mizbi, but it only works once.
I couldn't give the Dragon an [sic] riddle with no answer. Or one that I don't know the answer to. But what about a paradox?
If I scribed a grimoire that could create every possible grimoire, would it also create itself? That was my riddle. I gave her time to answer. Whatever answer she gave, I was able to argue against it. Our conversation ran in circles and at last, happily sated, she conceded.
My magic was forever altered. But I was already thinking ahead. I was thinking of you. When I said my farewell to the Scholarium, I told the Dragon about you. This was for your benefit, I promise. I told her three things:
I said that you would have a mind worthy of her riddles.
I said you would bring her what she asked for—a new impossible riddle.
And I said, very carefully, that you would never claim to be my inheritor.
Hopefully you see where this is headed. I have faith that you do. And if you don't, never be afraid to ask for help.
I've learned that we need not all struggle alone in pursuit of something as simple and joyous as a good riddle.